A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone with amino compounds

The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed re...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 10; no. 1; pp. 226 - 237
Main Authors Spagou, Konstantina, Malamidou-Xenikaki, Elizabeth, Spyroudis, Spyros
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 31.01.2005
MDPI
Subjects
2-hydroxy-1
4-naphthoquinone
Amines - chemistry
aminoesters
Carbon
Catalysis
Copper
Heterocyclic Compounds - chemical synthesis
Models, Biological
Naphthoquinones - chemistry
Onium Compounds - chemistry
Phenyliodonium ylides
ureas
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Summary:The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1420-3049
1420-3049
DOI:10.3390/10010226